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Bowl of roasted tomato soup with basil, served with a pesto grilled cheese on a tray in natural light.

Roasted Tomato Soup with Pesto Grilled Cheese

Roasted Tomato Soup with Pesto Grilled Cheese is the upgrade your classic tomato soup and grilled cheese never knew it needed. Roma tomatoes, onion, carrots, red pepper, and two whole heads of garlic are roasted until deeply caramelized and sweet. Then blended into a silky soup and served alongside a delicious pesto sourdough grilled cheese.
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Course: Main Course
Cuisine: Mediterranean
Keyword: tomato soup
Prep Time: 5 minutes
Cook Time: 1 hour
Servings: 5
Calories: 717kcal
Author: Lola Jay

Ingredients

Roasted tomato soup

Pesto grilled cheese

  • 8 slices sourdough bread
  • ¼ cup aioli
  • ½ cup pesto store bought or homemade
  • 2 cups sharp cheddar shredded
  • 1.5 cups mozzarella shredded
  • 1 tablespoon extra virgin olive oil

Instructions 

Roast the vegetables

  • Preheat your oven to 400F. Place the halved roma tomatoes cut side up, roughly chopped onion, carrot chunks, and red pepper pieces on a large sheet pan. Drizzle with the olive oil and balsamic vinegar. Sprinkle the garlic powder, onion powder, paprika, dried oregano, salt, red pepper flakes, and black pepper evenly over everything and toss to coat.
    10 roma tomatoes, 1 yellow onion, 2 carrots, 1 red pepper, 2 tbsp extra virgin olive oil, 1 tbsp balsamic vinegar, 2 tsp garlic powder, 2 tsp onion powder, 1 tsp paprika, 1 tbsp dried oregano, ½ tsp salt, ½ tsp red pepper flakes, ½ tsp black pepper
    Chopped vegetables with seasoning on a baking tray include tomatoes, onions, and carrots.
  • Cut the tops off both garlic bulbs to expose the cloves. Wrap them loosely in a piece of parchment paper and place cut side down on the sheet pan with the other vegetables.
    2 small garlic bulbs
    Preparing seasoned vegetables with spices and garlic for roasting on a sheet pan in a bright kitchen.
  • Roast at 400F for 45 to 50 minutes until the tomatoes are deeply caramelized and collapsing, the vegetables are tender and slightly charred at the edges, and the garlic is completely soft when pressed. Do not pull them early.
    Tray of roasted vegetables with tomatoes, onions, carrots, and garlic, in a kitchen setting with plants.

Build the soup

  • Heat a drizzle of olive oil in a large pot over medium heat. Add the tomato paste and cook for 1 to 2 minutes stirring constantly until it darkens slightly and smells sweet and rich rather than raw and tinny.
    2 tbsp tomato paste
    Stirring tomato paste into oil in a pot with a wooden spoon.
  • Add all of the roasted vegetables and any juices that accumulated on the sheet pan. Add the chicken bone broth and the roughly chopped fresh basil. Stir to combine and bring to a gentle simmer. Unwrap the roasted garlic and squeeze every single clove out of both heads directly into the pot. Cook for 5 minutes so the flavors come together.
    3 cups chicken bone broth, 6 fresh basil leaves
    Adding fresh garlic to a pot of tomato basil soup in a blue enamel pot.
  • Use an immersion blender to blend the soup directly in the pot until completely smooth and silky with no visible chunks. If using a standing blender, let the soup cool slightly, blend in batches with the lid slightly ajar, and return to the pot. Season with salt and pepper to taste.
    Blending tomato soup in a blue pot with an immersion blender.
  • Stir in the heavy cream and heat gently over medium low for 2 minutes until warmed through. Taste and adjust salt, pepper, and red pepper flakes as needed.
    ½ cup heavy cream
    Stirring cream into tomato soup in a pot with a wooden spoon, kitchen background.

Make the pesto grilled cheese

  • Spread aioli on the outside of all 8 sourdough slices. This is the side that will go face down in the pan. Spread pesto generously on the inside of 4 slices. Top the pesto with the shredded sharp cheddar and mozzarella divided evenly between the four sandwiches. Place the remaining 4 slices on top aioli side out.
    Spreading aioli on fresh sourdough bread slices in a kitchen setting with plants.
  • Heat a drizzle of olive oil in a large skillet over medium low heat. Place the sandwiches in the pan and cook for 3 to 4 minutes without pressing them down until the bottom is deeply golden and the aioli has crisped slightly. Flip carefully and cook for another 3 to 4 minutes until the second side is equally golden and the cheese is fully melted all the way through.
    8 slices sourdough bread, ¼ cup aioli, ½ cup pesto, 2 cups sharp cheddar, 1 tbsp extra virgin olive oil, 1.5 cups mozzarella
    Hand adding shredded cheese to pesto-covered bread in a pan for making a grilled cheese sandwich.
  • Remove from the pan and let it rest for 1 minute before cutting in half. The cheese needs that minute to set slightly so it does not all slide out the moment you cut it.
    Cheesy grilled cheese sandwich split open, with tomato soup in the background.

Serve

  • Ladle the roasted tomato soup into bowls and serve with the pesto grilled cheese alongside for dipping.
    Tomato soup with basil and grilled cheese sandwich.
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Notes

Nutrition facts are only estimates.
Storage
Store the soup in an airtight container in the refrigerator for up to 4 days or freeze for up to 3 months without the cream. Reheat gently on the stovetop, adding a splash of broth to loosen, and stir in fresh cream after reheating. Store grilled cheese sandwiches separately wrapped in the refrigerator for up to 1 day. Reheat in the air fryer at 375F for 4 minutes or in a pan over medium-low heat covered with a lid until the cheese is melted again. Avoid the microwave as it makes the bread soft and the cheese rubbery.

Nutrition

Calories: 717kcal | Carbohydrates: 62g | Protein: 36g | Fat: 57g | Saturated Fat: 23g | Polyunsaturated Fat: 3g | Monounsaturated Fat: 15g | Cholesterol: 104mg | Sodium: 987mg | Potassium: 887mg | Fiber: 6g | Sugar: 15g | Vitamin A: 7765IU | Vitamin C: 52mg | Calcium: 642mg | Iron: 6mg
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